WO2020189764A1 - 粘着剤組成物、粘着テープ、及び、電子部品の処理方法 - Google Patents
粘着剤組成物、粘着テープ、及び、電子部品の処理方法 Download PDFInfo
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- WO2020189764A1 WO2020189764A1 PCT/JP2020/012354 JP2020012354W WO2020189764A1 WO 2020189764 A1 WO2020189764 A1 WO 2020189764A1 JP 2020012354 W JP2020012354 W JP 2020012354W WO 2020189764 A1 WO2020189764 A1 WO 2020189764A1
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- adhesive composition
- general formula
- sensitive adhesive
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- OLAPPGSPBNVTRF-UHFFFAOYSA-N naphthalene-1,4,5,8-tetracarboxylic acid Chemical compound C1=CC(C(O)=O)=C2C(C(=O)O)=CC=C(C(O)=O)C2=C1C(O)=O OLAPPGSPBNVTRF-UHFFFAOYSA-N 0.000 description 1
- KQSABULTKYLFEV-UHFFFAOYSA-N naphthalene-1,5-diamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1N KQSABULTKYLFEV-UHFFFAOYSA-N 0.000 description 1
- DOBFTMLCEYUAQC-UHFFFAOYSA-N naphthalene-2,3,6,7-tetracarboxylic acid Chemical compound OC(=O)C1=C(C(O)=O)C=C2C=C(C(O)=O)C(C(=O)O)=CC2=C1 DOBFTMLCEYUAQC-UHFFFAOYSA-N 0.000 description 1
- XTBLDMQMUSHDEN-UHFFFAOYSA-N naphthalene-2,3-diamine Chemical compound C1=CC=C2C=C(N)C(N)=CC2=C1 XTBLDMQMUSHDEN-UHFFFAOYSA-N 0.000 description 1
- SXJVFQLYZSNZBT-UHFFFAOYSA-N nonane-1,9-diamine Chemical compound NCCCCCCCCCN SXJVFQLYZSNZBT-UHFFFAOYSA-N 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- WTSXICLFTPPDTL-UHFFFAOYSA-N pentane-1,3-diamine Chemical compound CCC(N)CCN WTSXICLFTPPDTL-UHFFFAOYSA-N 0.000 description 1
- FVDOBFPYBSDRKH-UHFFFAOYSA-N perylene-3,4,9,10-tetracarboxylic acid Chemical compound C=12C3=CC=C(C(O)=O)C2=C(C(O)=O)C=CC=1C1=CC=C(C(O)=O)C2=C1C3=CC=C2C(=O)O FVDOBFPYBSDRKH-UHFFFAOYSA-N 0.000 description 1
- JGGWKXMPICYBKC-UHFFFAOYSA-N phenanthrene-1,8,9,10-tetracarboxylic acid Chemical compound C1=CC=C(C(O)=O)C2=C(C(O)=O)C(C(O)=O)=C3C(C(=O)O)=CC=CC3=C21 JGGWKXMPICYBKC-UHFFFAOYSA-N 0.000 description 1
- VPRFQZSTJXHBHL-UHFFFAOYSA-N phenanthrene-9,10-diamine Chemical compound C1=CC=C2C(N)=C(N)C3=CC=CC=C3C2=C1 VPRFQZSTJXHBHL-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920003223 poly(pyromellitimide-1,4-diphenyl ether) Polymers 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 239000011112 polyethylene naphthalate Substances 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- QGOKIEUFWNCGFO-UHFFFAOYSA-N propanoic acid;pyrrole-2,5-dione Chemical compound CCC(O)=O.O=C1NC(=O)C=C1 QGOKIEUFWNCGFO-UHFFFAOYSA-N 0.000 description 1
- RTHVZRHBNXZKKB-UHFFFAOYSA-N pyrazine-2,3,5,6-tetracarboxylic acid Chemical compound OC(=O)C1=NC(C(O)=O)=C(C(O)=O)N=C1C(O)=O RTHVZRHBNXZKKB-UHFFFAOYSA-N 0.000 description 1
- JRDBISOHUUQXHE-UHFFFAOYSA-N pyridine-2,3,5,6-tetracarboxylic acid Chemical compound OC(=O)C1=CC(C(O)=O)=C(C(O)=O)N=C1C(O)=O JRDBISOHUUQXHE-UHFFFAOYSA-N 0.000 description 1
- 229920005604 random copolymer Polymers 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 150000000000 tetracarboxylic acids Chemical class 0.000 description 1
- LUEGQDUCMILDOJ-UHFFFAOYSA-N thiophene-2,3,4,5-tetracarboxylic acid Chemical compound OC(=O)C=1SC(C(O)=O)=C(C(O)=O)C=1C(O)=O LUEGQDUCMILDOJ-UHFFFAOYSA-N 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N titanium dioxide Inorganic materials O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J7/00—Adhesives in the form of films or foils
- C09J7/30—Adhesives in the form of films or foils characterised by the adhesive composition
- C09J7/38—Pressure-sensitive adhesives [PSA]
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J7/00—Adhesives in the form of films or foils
- C09J7/30—Adhesives in the form of films or foils characterised by the adhesive composition
- C09J7/35—Heat-activated
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/1003—Preparatory processes
- C08G73/1007—Preparatory processes from tetracarboxylic acids or derivatives and diamines
- C08G73/101—Preparatory processes from tetracarboxylic acids or derivatives and diamines containing chain terminating or branching agents
- C08G73/1014—Preparatory processes from tetracarboxylic acids or derivatives and diamines containing chain terminating or branching agents in the form of (mono)anhydrid
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
- C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
- C08F290/06—Polymers provided for in subclass C08G
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G73/1042—Copolyimides derived from at least two different tetracarboxylic compounds or two different diamino compounds
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G73/1046—Polyimides containing oxygen in the form of ether bonds in the main chain
- C08G73/105—Polyimides containing oxygen in the form of ether bonds in the main chain with oxygen only in the diamino moiety
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G73/1075—Partially aromatic polyimides
- C08G73/1082—Partially aromatic polyimides wholly aromatic in the tetracarboxylic moiety
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/12—Unsaturated polyimide precursors
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G73/12—Unsaturated polyimide precursors
- C08G73/121—Preparatory processes from unsaturated precursors and polyamines
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/12—Unsaturated polyimide precursors
- C08G73/125—Unsaturated polyimide precursors the unsaturated precursors containing atoms other than carbon, hydrogen, oxygen or nitrogen in the main chain
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
- C09J11/02—Non-macromolecular additives
- C09J11/06—Non-macromolecular additives organic
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J179/00—Adhesives based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen, with or without oxygen, or carbon only, not provided for in groups C09J161/00 - C09J177/00
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- C09J179/00—Adhesives based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen, with or without oxygen, or carbon only, not provided for in groups C09J161/00 - C09J177/00
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- C09J179/085—Unsaturated polyimide precursors
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- C09J4/00—Adhesives based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; adhesives, based on monomers of macromolecular compounds of groups C09J183/00 - C09J183/16
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- C09J5/00—Adhesive processes in general; Adhesive processes not provided for elsewhere, e.g. relating to primers
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
- H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
- H01L21/04—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer
- H01L21/18—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer the devices having semiconductor bodies comprising elements of Group IV of the Periodic Table or AIIIBV compounds with or without impurities, e.g. doping materials
- H01L21/30—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26
- H01L21/302—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26 to change their surface-physical characteristics or shape, e.g. etching, polishing, cutting
- H01L21/304—Mechanical treatment, e.g. grinding, polishing, cutting
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
- H01L21/67—Apparatus specially adapted for handling semiconductor or electric solid state devices during manufacture or treatment thereof; Apparatus specially adapted for handling wafers during manufacture or treatment of semiconductor or electric solid state devices or components ; Apparatus not specifically provided for elsewhere
- H01L21/683—Apparatus specially adapted for handling semiconductor or electric solid state devices during manufacture or treatment thereof; Apparatus specially adapted for handling wafers during manufacture or treatment of semiconductor or electric solid state devices or components ; Apparatus not specifically provided for elsewhere for supporting or gripping
- H01L21/6835—Apparatus specially adapted for handling semiconductor or electric solid state devices during manufacture or treatment thereof; Apparatus specially adapted for handling wafers during manufacture or treatment of semiconductor or electric solid state devices or components ; Apparatus not specifically provided for elsewhere for supporting or gripping using temporarily an auxiliary support
- H01L21/6836—Wafer tapes, e.g. grinding or dicing support tapes
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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- C09J2203/00—Applications of adhesives in processes or use of adhesives in the form of films or foils
- C09J2203/326—Applications of adhesives in processes or use of adhesives in the form of films or foils for bonding electronic components such as wafers, chips or semiconductors
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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- C09J2301/00—Additional features of adhesives in the form of films or foils
- C09J2301/40—Additional features of adhesives in the form of films or foils characterized by the presence of essential components
- C09J2301/416—Additional features of adhesives in the form of films or foils characterized by the presence of essential components use of irradiation
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J2301/00—Additional features of adhesives in the form of films or foils
- C09J2301/50—Additional features of adhesives in the form of films or foils characterized by process specific features
- C09J2301/502—Additional features of adhesives in the form of films or foils characterized by process specific features process for debonding adherents
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J2433/00—Presence of (meth)acrylic polymer
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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- C09J2479/00—Presence of polyamine or polyimide
- C09J2479/08—Presence of polyamine or polyimide polyimide
-
- H—ELECTRICITY
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- H01L2221/683—Apparatus for handling semiconductor or electric solid state devices during manufacture or treatment thereof; Apparatus for handling wafers during manufacture or treatment of semiconductor or electric solid state devices or components; Apparatus not specifically provided for elsewhere for supporting or gripping
- H01L2221/68304—Apparatus for handling semiconductor or electric solid state devices during manufacture or treatment thereof; Apparatus for handling wafers during manufacture or treatment of semiconductor or electric solid state devices or components; Apparatus not specifically provided for elsewhere for supporting or gripping using temporarily an auxiliary support
- H01L2221/68327—Apparatus for handling semiconductor or electric solid state devices during manufacture or treatment thereof; Apparatus for handling wafers during manufacture or treatment of semiconductor or electric solid state devices or components; Apparatus not specifically provided for elsewhere for supporting or gripping using temporarily an auxiliary support used during dicing or grinding
-
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- H01L2221/683—Apparatus for handling semiconductor or electric solid state devices during manufacture or treatment thereof; Apparatus for handling wafers during manufacture or treatment of semiconductor or electric solid state devices or components; Apparatus not specifically provided for elsewhere for supporting or gripping
- H01L2221/68304—Apparatus for handling semiconductor or electric solid state devices during manufacture or treatment thereof; Apparatus for handling wafers during manufacture or treatment of semiconductor or electric solid state devices or components; Apparatus not specifically provided for elsewhere for supporting or gripping using temporarily an auxiliary support
- H01L2221/68381—Details of chemical or physical process used for separating the auxiliary support from a device or wafer
Definitions
- the present invention relates to a method for treating an adhesive composition, an adhesive tape, and an electronic component.
- the electronic components When processing electronic components such as semiconductors, in order to facilitate the handling of the electronic components and prevent them from being damaged, the electronic components are fixed to the support plate via an adhesive composition, or the adhesive tape is electronically attached. It is protected by sticking it on parts.
- the thick film wafer cut out from a high-purity silicon single crystal or the like is ground to a predetermined thickness to obtain a thin film wafer, the thick film wafer can be adhered to a support plate via an adhesive composition. Will be done.
- Patent Document 1 discloses a pressure-sensitive adhesive sheet in which a polyfunctional monomer or oligomer having a radiopolymerizable functional group is bonded to the side chain or main chain of a polymer. Has been done.
- the adhesive strength is lowered by irradiating ultraviolet rays at the time of peeling, and peeling can be performed without adhesive residue.
- a metal thin film having more excellent conductivity can be formed by processing at a high temperature of about 300 to 350 ° C.
- a high-temperature processing treatment at 300 ° C. or higher, the adhesion is enhanced and the adhesive strength is not sufficiently reduced at the time of peeling, or glue is used. The rest may occur.
- the present invention is a pressure-sensitive adhesive composition that can be easily peeled off by irradiating light even after undergoing a high-temperature processing treatment of 300 ° C. or higher with the adherend fixed.
- An object of the present invention is to provide an adhesive tape having an adhesive layer made of the adhesive composition, and a method for treating electronic components.
- the present invention is a pressure-sensitive adhesive composition containing a reactive resin having an imide skeleton in the main chain and a functional group having a double bond in the side chain or the terminal, and a silicone compound or a fluorine compound.
- a reactive resin having an imide skeleton in the main chain and a functional group having a double bond in the side chain or the terminal and a silicone compound or a fluorine compound.
- the pressure-sensitive adhesive composition according to one embodiment of the present invention is a reactive resin having an imide skeleton in the main chain and a functional group having a double bond in the side chain or the terminal (hereinafter, also simply referred to as “reactive resin”). ) Is included. Since the reactive resin has an imide skeleton in the main chain, it has extremely excellent heat resistance, and even after undergoing a high-temperature processing treatment of 300 ° C. or higher, the main chain is less likely to be decomposed and adhesion is enhanced. , It is possible to prevent adhesive residue from being generated at the time of peeling.
- the reactive resin has a functional group having a double bond at the side chain or the terminal, the entire pressure-sensitive adhesive composition is uniformly and quickly polymerized and crosslinked by irradiation with light, and the elastic modulus is increased. As a result, the adhesive strength is greatly reduced, and the material can be easily peeled off.
- Examples of the functional group having a double bond existing in the side chain or the terminal of the reactive resin include a maleimide group, a citraconimide group, a vinyl ether group, an allyl group, and a (meth) acrylic group which may be substituted. Be done. Of these, a maleimide group that may be substituted is preferable because higher heat resistance can be obtained.
- the reactive resin preferably has a functional group equivalent having a double bond (weight average molecular weight / number of functional groups having a double bond) of 4000 or less.
- the functional group equivalent is 4000 or less, the pressure-sensitive adhesive composition can exhibit higher heat resistance. It is considered that this is because having a functional group having a double bond at a certain density or higher in the molecule of the reactive resin shortens the distance between the crosslinks, thereby further suppressing the enhancement of adhesion due to heating.
- the functional group equivalent is more preferably 3000 or less, and further preferably 2000 or less.
- the lower limit of the functional group equivalent is not particularly limited, but is substantially about 600 as the lower limit.
- the reactive resin preferably has a weight average molecular weight of 5000 or more.
- the weight average molecular weight of the reactive resin is 5000 or more, film formation becomes easy and the obtained film exhibits a certain degree of flexibility, so that the adherend having irregularities is highly followed. It can exhibit its properties and can be easily peeled off from the adherend.
- the weight average molecular weight of the reactive resin is more preferably 10,000 or more, and further preferably 20,000 or more.
- the upper limit of the weight average molecular weight of the reactive resin is not particularly limited, but is, for example, 300,000, particularly 100,000 because the solubility in a solvent is low.
- the weight average molecular weight of the reactive resin is measured as a polystyrene-equivalent molecular weight by a gel permeation chromatography (GPC) method.
- GPC gel permeation chromatography
- HR-MB-M product name, manufactured by Waters
- the functional group having the double bond may be on either the side chain or the terminal of the reactive resin.
- the functional group having the double bond is preferably present at both ends of the reactive resin, and more preferably in the side chain in addition to both ends.
- the functional groups having double bonds at both ends of the reactive resin are highly reactive, and the pressure-sensitive adhesive composition can be more sufficiently cured by irradiation with light. As a result, the enhancement of adhesion can be further suppressed, and the pressure-sensitive adhesive composition can exhibit higher heat resistance. Further, the pressure-sensitive adhesive composition can exhibit higher heat resistance by having a functional group having a double bond in the side chain of the reactive resin. It is considered that this is because the adhesion enhancement due to heating is further suppressed by shortening the distance between the crosslinks.
- the side chain of the reactive resin has a functional group having a double bond, it becomes easy to adjust the functional group equivalent to 4000 or less while setting the weight average molecular weight to 5000 or more.
- the pressure-sensitive adhesive composition has sufficient initial adhesive strength, and at the same time, has excellent heat resistance, and even if it is subjected to a high-temperature processing treatment of 300 ° C. or higher, there is little adhesion enhancement, and it can be peeled off more easily by irradiating with light. can do.
- the reactive resin is represented by, for example, a structural unit represented by the following general formula (1a), a structural unit represented by the following general formula (1b), and the following general formula (1c).
- Examples thereof include a reactive resin (1) having a structural unit (where s ⁇ 1, t ⁇ 0, u ⁇ 0) and whose ends are represented by X 1 and X 2 , respectively.
- P 1 , P 2 and P 3 each independently represent an aromatic group
- Q 1 is a substituted or unsubstituted linear, branched chain or represents a cyclic aliphatic group
- Q 2 represents a group having a substituted or unsubstituted aromatic structure
- R represents a substituted or unsubstituted branched-chain aliphatic group or an aromatic group.
- At least one selected from the group consisting of X 1 , X 2 and X 3 represents a functional group having a double bond.
- P 1 , P 2 , and P 3 are preferably aromatic groups having 5 to 50 carbon atoms. Since P 1 , P 2 , and P 3 are aromatic groups having 5 to 50 carbon atoms, the pressure-sensitive adhesive composition according to one embodiment of the present invention can exhibit particularly high heat resistance.
- Q 1 is a substituted or unsubstituted, straight, is preferably a branched or cyclic aliphatic group having a carbon number of 2 to 100.
- the tape can exhibit high flexibility, can exhibit high followability to an adherend having irregularities, and also improves peelability.
- Q 1 is preferably an aliphatic group derived from a diamine compound as described later. Among them, in view of flexibility, and, from the viewpoint of manufacturing compatibility increases the adhesive tape with a solvent or other components of the reactive resin (1) is facilitated, Q 1 is derived from dimer diamine It is preferably an aliphatic group.
- the aliphatic group derived from the diamine diamine is not particularly limited, but is a group represented by the following general formula (4-1), a group represented by the following general formula (4-2), and the following general formula (4-3). ), And at least one selected from the group consisting of the groups represented by the following general formula (4-4). Among them, the group represented by the following general formula (4-2) is more preferable.
- R 1 to R 8 and R 13 to R 20 each independently represent a linear or branched hydrocarbon group. Note that * represents a bond. That is, * is combined with N in the above general formulas (1a) to (1c).
- the hydrocarbon groups represented by R 1 to R 8 and R 13 to R 20 are not particularly limited and may be saturated hydrocarbon groups. It may be an unsaturated hydrocarbon group. Among them, R 1 and R 2, R 3 and R 4, R 5 and R 6, R 7 and R 8, R 13 and R 14, R 15 and R 16, R 17 and R 18, and, with R 19 It is preferable that the total number of carbon atoms of R 20 is 7 or more and 50 or less. When the total number of carbon atoms is within the above range, the adhesive tape produced by using the pressure-sensitive adhesive composition according to the embodiment of the present invention can exhibit higher flexibility, and the above-mentioned reactivity can be exhibited.
- the compatibility of the resin (1) with the solvent and other components is further increased.
- the total number of carbon atoms is more preferably 9 or more, still more preferably 12 or more, and even more preferably 14 or more.
- the total number of carbon atoms is more preferably 35 or less, still more preferably 25 or less, and even more preferably 18 or less.
- the optical isomerism of the group represented by 4) is not particularly limited, and any optical isomerism is included.
- Q 2 is preferably a group having an aromatic structure of a substituted or unsubstituted 5 to 50 carbon atoms.
- Q 2 is a group having an aromatic structure of a substituted or unsubstituted 5 to 50 carbon atoms, the pressure-sensitive adhesive composition which is an embodiment of the present invention can exhibit a particularly high heat resistance.
- R is preferably a substituted or unsubstituted branched chain-like aliphatic group or aromatic group having 2 to 100 carbon atoms. Since R is a substituted or unsubstituted branched chain-like aliphatic group or aromatic group having 2 to 100 carbon atoms, the adhesive tape produced by using the pressure-sensitive adhesive composition according to one embodiment of the present invention is expensive. It is possible to exhibit flexibility, exhibit high followability to an adherend having irregularities, and improve peelability.
- R is the an aromatic group having an aromatic ester group or an aromatic ether group, aromatic ester or aromatic ether groups in R is bonded to X 3 Is preferable.
- aromatic ester group means a group in which an ester group is directly bonded to an aromatic ring
- aromatic ether group means a group in which an ether group is directly bonded to an aromatic ring. ..
- the functional group having a double bond may be at least one selected from the group consisting of X 1 , X 2 and X 3, but at least one. It is preferable that X 3 is a functional group having a double bond. When at least X 3 is a functional group having a double bond, the pressure-sensitive adhesive composition can exhibit higher heat resistance. When any of the above X 1 , X 2 and X 3 is a functional group other than a functional group having a double bond (a functional group having no double bond), the functional group does not have the double bond.
- an aliphatic group, an alicyclic group, an aromatic group, an acid anhydride, an amine compound and the like can be mentioned.
- Specific examples thereof include an acid anhydride used as a raw material for the reactive resin (1) and a one-ended unreacted product of a diamine compound.
- the functional group having a double bond in the reactive resin (1) include a maleimide group, a citraconimide group, a vinyl ether group, an allyl group, and a (meth) acrylic group which may be substituted.
- a maleimide group or an allyl group that may be substituted is preferable because higher heat resistance can be obtained, and a tri (iso) cyanurate having one or more allyl groups can be obtained because particularly high adhesiveness can be obtained. Groups are more preferred.
- s is 1 or more, preferably 3 or more, preferably 10 or less, and more preferably 5 or less.
- t is 0 or more, preferably 1 or more, more preferably 3 or more, preferably 10 or less, and more preferably 5 or less.
- u is 0 or more, preferably 1 or more, more preferably 3 or more, preferably 10 or less, and more preferably 5 or less.
- the unit may be a block copolymer composed of block components in which each structural unit is continuously arranged, or may be a random copolymer in which each structural unit is randomly arranged.
- an imide compound is prepared by reacting a diamine compound with an aromatic acid anhydride, and further, the functional group of the imide compound is double-bonded with a functional group that reacts with the functional group. It can be obtained by reacting with a compound having a functional group (hereinafter, referred to as a functional group-containing unsaturated compound).
- the diamine compound either an aliphatic diamine compound or an aromatic diamine compound can be used.
- an aliphatic diamine compound as the diamine compound, the adhesive tape produced by using the pressure-sensitive adhesive composition according to the embodiment of the present invention can exhibit high flexibility, and an adherend having irregularities can be obtained. On the other hand, high followability can be exhibited and peelability is also improved.
- an aromatic diamine compound as the diamine compound, the heat resistance of the pressure-sensitive adhesive composition according to the embodiment of the present invention is further improved.
- a diamine compound having a functional group is used as the diamine compound, and the functional group is reacted with the functional group-containing unsaturated compound to produce a reactive resin having a functional group having a double bond in the side chain. can do.
- These aliphatic diamine compounds, aromatic diamine compounds and diamine compounds having a functional group may be used alone or in combination of two or more.
- Examples of the aliphatic diamine compound include 1,10-diaminodecane, 1,12-diaminododecane, dimerdiamine, 1,2-diamino-2-methylpropane, 1,2-diaminocyclohexane, and 1,2-diamino.
- aromatic diamine compound examples include 9,10-diaminophenanthrene, 4,4'-diaminooctafluorobiphenyl, 3,7-diamino-2-methoxyfluorene, 4,4'-diaminobenzophenone, and 3,4-.
- Diaminobenzophenone 3,4-diaminotoluene, 2,6-diaminoanthraquinone, 2,6-diaminotoluene, 2,3-diaminotoluene, 1,8-diaminonaphthalene, 2,4-diaminotoluene, 2,5-diamino Toluene, 1,4-diaminoanthraquinone, 1,5-diaminoanthraquinone, 1,5-diaminonaphthalene, 1,2-diaminoanthraquinone, 2,4-cumendiamine, 1,3-bisaminomethylbenzene, 1,3- Bisaminomethylcyclohexane, 2-chloro-1,4-diaminobenzene, 1,4-diamino-2,5-dichlorobenzene, 1,4-diamino-2,5-dimethylbenzene, 4,4'
- dimer diamine is preferable from the viewpoint of increasing the flexibility and from the viewpoint of increasing the compatibility of the reactive resin with the solvent and other components and facilitating the production of the adhesive tape.
- the diamine diamine is a diamine compound obtained by reducing and amination of cyclic and acyclic diamine acids obtained as dimers of unsaturated fatty acids, and is, for example, a linear type, a monocyclic type, or a polycyclic type. Examples include diamine diamines such as molds.
- the dimer diamine may contain a carbon-carbon unsaturated double bond, or may be a hydrogenated additive to which hydrogen has been added.
- the diamine diamine is represented by, for example, a group represented by the above-mentioned general formula (4-1), a group represented by the general formula (4-2), and a general formula (4-3).
- Examples thereof include a diamine diamine capable of forming a group represented by the general formula (4-4).
- Examples of the diamine compound having a functional group include a diamine compound having a hydroxyl group, a diamine compound having a carboxyl group, and a diamine compound having a halogen group.
- Examples of the diamine compound having a hydroxyl group include 1,3-diamino-2-propanol, 2,4-diaminophenoxyethanol, 3,5-diaminophenoxyethanol, 2,4-diaminophenol, 3,5-diaminophenol, and 2, , 4-Diaminobenzyl alcohol, 4,6-diaminoresorcin dihydrochloride, 2,2-bis (3-amino-4-hydroxyphenyl) hexafluoropropane and the like.
- Examples of the diamine compound having a carboxyl group include 3,5-diaminobenzoic acid and the like.
- Examples of the diamine compound having a halogen group include 2,4-diaminochlorobenzene and the like.
- aromatic acid anhydride examples include pyromellitic acid, 1,2,5,6-naphthalenetetracarboxylic acid, 2,3,6,7-naphthalenetetracarboxylic acid, 1,2,4,5-naphthalene. Tetracarboxylic acid, 1,4,5,8-naphthalenetetracarboxylic acid, 3,3', 4,4'-benzophenone tetracarboxylic acid, 3,3', 4,4'-biphenyl ether tetracarboxylic acid, 3, 3', 4,4'-biphenyltetracarboxylic acid, 2,3,5,6-pyridinetetracarboxylic acid, 3,4,9,10-perylenetetracarboxylic acid, 4,4'-sulfonyldiphthalic acid, 1 -Trifluoromethyl-2,3,5,6-benzenetetracarboxylic acid, 2,2', 3,3'-biphenyltetracarboxylic acid,
- the functional group-containing unsaturated compound is selected and used according to the functional group at the terminal or side chain of the imide compound.
- a maleimide compound having a carboxyl group can be mentioned.
- the maleimide compound having a carboxyl group include maleimide acetate, maleimide propionic acid, maleimide butyric acid, maleimide hexane acid, trans-4- (N-maleimide methyl) cyclohexane-1-carboxylic acid, and 19-maleimide-17-oxo. -4,7,10,13-tetraoxa-16-azanonadecanic acid and the like can be mentioned.
- vinyl compounds having an ether group such as butyl vinyl ether, allyl compounds having a glycidyl group such as diallyl monoglycidyl isocyanurate, allyl ether compounds having a glycidyl group such as allyl glycidyl ether and glycerin diallyl monoglycidyl ether can be mentioned.
- vinyl ether compounds having a glycidyl group such as glycidyl oxyethyl vinyl ether, glycidyl oxybutyl vinyl ether, glycidyl oxyhexyl vinyl ether, glycidyl diethylene glycol vinyl ether and glycidyl cyclohexanedimethanol monovinyl ether can be mentioned.
- allyl compounds having an isocyanate group such as allyl isocyanate, (meth) acryloyl compounds having an isocyanate group such as 2- (meth) acryloyloxyethyl isocyanate and the like can be mentioned.
- an allyl compound having a hydroxyl group such as trimethylolpropane diallyl ether or pentaerythritol triallyl ether, or glycidyl such as diallyl monoglycidyl isocyanurate.
- allyl compounds having a group include allyl compounds having a group.
- allyl ether compounds having a glycidyl group such as allyl glycidyl ether and glycerin diallyl monoglycidyl ether can be mentioned.
- vinyl ether compounds having a glycidyl group such as glycidyl oxyethyl vinyl ether, glycidyl oxybutyl vinyl ether, glycidyl oxyhexyl vinyl ether, glycidyl diethylene glycol vinyl ether and glycidyl cyclohexanedimethanol monovinyl ether can be mentioned.
- the pressure-sensitive adhesive composition according to one embodiment of the present invention contains a silicone compound or a fluorine compound. Since the silicone compound and the fluorine compound have excellent heat resistance, they prevent the pressure-sensitive adhesive composition from being scorched even after undergoing a high-temperature processing process of 300 ° C. or higher, and bleed out to the interface of the adherend during peeling, facilitating peeling. To do.
- the silicone compound is not particularly limited, and examples thereof include silicone oil, silicone diacrylate, and silicone-based graft copolymer.
- the fluorine compound is not particularly limited, and examples thereof include a hydrocarbon compound having a fluorine atom.
- the silicone compound or fluorine compound preferably has a functional group that can be crosslinked with the reactive resin. Since the silicone compound or the fluorine compound has a functional group capable of cross-linking with the reactive resin, the silicone compound or the fluorine compound chemically reacts with the reactive resin by light irradiation at the time of peeling or the like, and is contained in the reactive resin. Since it is incorporated into the adherend, it is possible to prevent the silicone compound or the fluorine compound from adhering to the adherend and contaminating the adherend.
- the functional group crosslinkable with the above reactive resin is not particularly limited, for example, a carboxy group, a radically polymerizable unsaturated bond (for example, a vinyl group, a (meth) acryloyl group, a optionally substituted maleimide group), a hydroxy.
- a radically polymerizable unsaturated bond for example, a vinyl group, a (meth) acryloyl group, a optionally substituted maleimide group
- a hydroxy examples thereof include a group, an amide group, an isocyanate group and an epoxy group.
- a silicone compound having a crosslinkable functional group with the above-mentioned reactive resin is preferable from the viewpoint of being environmentally friendly and easy to dispose of.
- silicone compound having a functional group that can be crosslinked with the reactive resin a silicone compound having a siloxane skeleton in the main chain and a functional group having a double bond in the side chain or the terminal is preferable.
- the silicone compound having a siloxane skeleton in the main chain and a functional group having a double bond at the side chain or the terminal is not particularly limited, but the silicone compound represented by the following general formula (I) and the following general formula (II). ), And at least one selected from the group consisting of the silicone compound represented by the following general formula (III).
- These silicone compounds have particularly high heat resistance and high polarity, so that they can easily bleed out from the pressure-sensitive adhesive composition.
- X and Y each independently represent an integer of 0 to 1200, and R represents a functional group having a double bond.
- examples of the functional group having a double bond represented by R include a maleimide group, a citraconimide group, and a vinyl ether which may be substituted. Examples include groups, allyl groups, (meth) acrylic groups and the like. Of these, a maleimide group that may be substituted is preferable because higher heat resistance can be obtained.
- the plurality of Rs when a plurality of Rs exist, the plurality of Rs may be the same or different.
- silicone compounds having a (meth) acrylic group in the siloxane skeleton represented by the general formula (I), general formula (II), and general formula (III) commercially available silicone compounds are, for example, EBECRYL350 and EBECRYL1360 All of them are manufactured by Daicel Cytec Co., Ltd.). Further, BYK-UV3500 (manufactured by BIC Chemie), TEGO RAD2250 (manufactured by Evonik) (all R is an acrylic group) and the like can be mentioned.
- the content of the silicone compound or the fluorine compound in the pressure-sensitive adhesive composition according to one embodiment of the present invention is not particularly limited, but the preferable lower limit is 0.1 parts by weight and the preferable upper limit is 20 parts by weight with respect to 100 parts by weight of the reactive resin. It is a part by weight.
- the content of the silicone compound or the fluorine compound is within this range, the pressure-sensitive adhesive composition can exhibit excellent peelability without contaminating the adherend.
- the more preferable lower limit of the content of the silicone compound or the fluorine compound is 0.3 parts by weight, and the more preferable upper limit is 10 parts by weight.
- the pressure-sensitive adhesive composition according to one embodiment of the present invention has excellent heat resistance, a sufficient effect can be exhibited even if the content of the silicone compound or the fluorine compound is relatively small. Therefore, the possibility of contamination by the silicone compound or the fluorine compound can be further reduced.
- the pressure-sensitive adhesive composition according to an embodiment of the present invention further has a polyfunctional monomer or a polyfunctional oligomer having two or more functional groups having a double bond in the molecule and having a molecular weight of 5000 or less (hereinafter, simply ". Also referred to as "polyfunctional monomer or polyfunctional oligomer").
- a polyfunctional monomer or a polyfunctional oligomer having two or more functional groups having a double bond in the molecule and having a molecular weight of 5000 or less.
- Examples of the functional group having a double bond in the polyfunctional monomer or the polyfunctional oligomer include a maleimide group, a citraconimide group, a vinyl ether group, an allyl group, and a (meth) acrylic group which may be substituted.
- a maleimide group that may be substituted is preferable because higher heat resistance can be obtained.
- the content of the polyfunctional monomer or polyfunctional oligomer in the pressure-sensitive adhesive composition according to one embodiment of the present invention is not particularly limited, but a total of 100 parts by weight of the reactive resin and the polyfunctional monomer or polyfunctional oligomer is used.
- the preferable lower limit is 5 parts by weight
- the preferable upper limit is 100 parts by weight.
- the pressure-sensitive adhesive composition can exhibit particularly excellent peelability. From the viewpoint of further enhancing the peelability, the more preferable lower limit of the content of the polyfunctional monomer or the polyfunctional oligomer is 10 parts by weight, and the more preferable upper limit is 50 parts by weight.
- the pressure-sensitive adhesive composition according to one embodiment of the present invention preferably further contains a photopolymerization initiator.
- the photopolymerization initiator include those that are activated by irradiating light having a wavelength of 250 to 800 nm.
- the photopolymerization initiator include acetphenone derivative compounds such as methoxyacetophenone, benzoin ether compounds such as benzoin propyl ether and benzoin isobutyl ether, ketal derivative compounds such as benzyl dimethyl ketal and acetophenone diethyl ketal, and phosphine oxide derivative compounds. And so on.
- photoradical polymerization of bis ( ⁇ 5-cyclopentadienyl) titanosen derivative compound, benzophenone, Michler ketone, chlorothioxanthone, dodecylthioxanthone, dimethylthioxanthone, diethylthioxanthone, ⁇ -hydroxycyclohexylphenylketone, 2-hydroxymethylphenylpropane, etc. is started. Agents are mentioned.
- These photopolymerization initiators may be used alone or in combination of two or more.
- the content of the photopolymerization initiator in the pressure-sensitive adhesive composition according to one embodiment of the present invention is not particularly limited, but the preferable lower limit is 0.1 parts by weight and the preferable upper limit is 10 parts by weight with respect to 100 parts by weight of the reactive resin. It is a department. When the content of the photopolymerization initiator is within this range, the entire pressure-sensitive adhesive composition is uniformly and quickly polymerized and crosslinked by irradiation with light, and the elastic modulus is increased, so that the adhesive strength is greatly reduced. Then, it can be easily peeled off.
- the more preferable lower limit of the content of the photopolymerization initiator is 0.3 parts by weight, and the more preferable upper limit is 3 parts by weight.
- the pressure-sensitive adhesive composition according to one embodiment of the present invention may further contain a gas generating agent that generates a gas by irradiating with light.
- a gas generating agent that generates a gas by irradiating with light.
- gas generator examples include a tetrazole compound or a salt thereof, a triazole compound or a salt thereof, an azo compound, an azide compound, xanthone acetic acid, a carbonate and the like. These gas generators may be used alone or in combination of two or more. Of these, a tetrazole compound or a salt thereof is preferable because it is particularly excellent in heat resistance.
- the content of the gas generating agent in the pressure-sensitive adhesive composition according to one embodiment of the present invention is not particularly limited, but the preferable lower limit is 5 parts by weight and the preferable upper limit is 50 parts by weight with respect to 100 parts by weight of the reactive resin. ..
- the pressure-sensitive adhesive composition can exhibit particularly excellent peelability.
- the more preferable lower limit of the content of the gas generating agent is 8 parts by weight, and the more preferable upper limit is 30 parts by weight.
- the pressure-sensitive adhesive composition according to one embodiment of the present invention is known as, for example, a photosensitizer, a heat stabilizer, an antioxidant, an antistatic agent, a plasticizer, a resin, a surfactant, a wax, a fine particle filler, and the like. Additives may be included.
- the fine particle filler examples include oxides of silicon, titanium, aluminum, calcium, boron, magnesium and zirconia, and an inorganic filler consisting of at least one selected from the group consisting of composites thereof.
- silicon-aluminum-boron composite oxide, silicon-titanium composite oxide, and silica-titania composite oxide are preferable because they have physical properties similar to those of silica generally used as an inorganic filler.
- the average particle size of the inorganic filler is not particularly limited, but a preferable lower limit is 0.1 ⁇ m and a preferable upper limit is 30 ⁇ m.
- the content of the inorganic filler is not particularly limited, but the preferable lower limit is 30 parts by weight and the preferable upper limit is 150 parts by weight with respect to 100 parts by weight of the reactive resin.
- the more preferable lower limit of the content of the inorganic filler is 60 parts by weight, and the more preferable upper limit is 120 parts by weight.
- the method for producing the pressure-sensitive adhesive composition according to one embodiment of the present invention is not particularly limited, and for example, the above-mentioned reactive resin, silicone compound or fluorine compound and an additive to be blended as necessary are mixed with a bead mill or ultrasonic waves. Examples thereof include a method of mixing using a dispersion, a homogenizer, a high-power dispar, a roll mill, or the like.
- An adhesive tape having an adhesive layer composed of an adhesive composition according to an embodiment of the present invention is also one of the present inventions.
- the adhesive tape according to the embodiment of the present invention may be a support tape having an adhesive layer composed of the adhesive composition according to the embodiment of the present invention on one or both surfaces of the base material. It may be a non-support tape having no material.
- the base material examples include sheets made of transparent resins such as acrylic, olefin, polycarbonate, vinyl chloride, ABS, polyethylene terephthalate (PET), polyethylene naphthalate (PEN), nylon, urethane and polyimide. Further, a sheet having a mesh-like structure, a sheet having holes, and the like can also be used.
- transparent resins such as acrylic, olefin, polycarbonate, vinyl chloride, ABS, polyethylene terephthalate (PET), polyethylene naphthalate (PEN), nylon, urethane and polyimide.
- the pressure-sensitive adhesive composition and the pressure-sensitive adhesive tape according to one embodiment of the present invention have initial adhesive strength, are excellent in heat resistance, and are less likely to be adherent even when processed at a high temperature of 300 ° C. or higher, and are irradiated with light. Can be easily peeled off. Since the pressure-sensitive adhesive composition and the pressure-sensitive adhesive tape according to one embodiment of the present invention are particularly excellent in heat resistance, they can be suitably used for protecting and temporarily fixing an adherend that is subjected to a high-temperature processing treatment of 300 ° C. or higher. In particular, when processing electronic components such as semiconductors, in order to facilitate the handling of the electronic components and prevent them from being damaged, the electronic components may be fixed to the support plate via an adhesive composition or an adhesive tape. The adhesive tape can be suitably used for protecting electronic components by attaching them.
- Examples thereof include a method for processing an electronic component, which includes a step of peeling the electronic component.
- Such a method for processing electronic components is also one of the present inventions.
- the step of irradiating the adhesive tape with light may be performed immediately before the step of peeling the adhesive tape from the electronic component, but after the step of temporarily fixing the electronic component on the adhesive tape, the electronic component is heat-treated. It is preferable to carry out before the step of carrying out. By performing the step of irradiating the adhesive tape with light before the step of heat-treating the electronic component, the adhesive tape can exhibit more excellent heat resistance.
- an adhesive composition which can be easily peeled off by irradiating light even after undergoing a high temperature processing treatment of 300 ° C. or higher with the adherend fixed. It is possible to provide an adhesive tape having an adhesive layer composed of a composition, and a method for processing an electronic component.
- a Dean-Stark trap and condenser were attached to the flask and the mixture was refluxed for 2 hours to form amine-terminated diimides. After cooling the reaction product to room temperature or lower, 12.8 g (0.13 mol) of maleic anhydride was added, and then 5 g (0.05 mol) of methanesulfonic acid anhydride was added. After refluxing the mixture for another 12 hours, the mixture was cooled to room temperature, 300 mL of toluene was added to the flask, and impurities were precipitated and removed by standing. The obtained solution is filtered through a glass frit funnel filled with silica gel, and then the solvent is removed by vacuum.
- the solution is amber wax-like, has an imide skeleton in the main chain, and has maleimide groups at both ends.
- the reactive resin 1 represented by -1) was obtained.
- the obtained reactive resin 1 was measured by a gel permeation chromatography (GPC) method using THF as an eluent and HR-MB-M (trade name, manufactured by Waters) as a column, and the weight average molecular weight was 5000. there were.
- Reactive Resin 2 250 mL of toluene was put into a 500 mL round bottom flask containing a Teflon (registered trademark) stirrer. Then, 35 g (0.35 mol) of triethylamine and 35 g (0.36 mol) of anhydrous methanesulfonic acid were added and stirred to form a salt. After stirring for 10 minutes, 28 g (0.05 mol) of dimer diamine (Priamine 1075 manufactured by Claude), 4.5 g (0.05 mol) of 1,3-diamino-2-propanol, and pyromellitic anhydride 21. 8 g (0.1 mol) was added in this order.
- Teflon registered trademark
- a Dean-Stark tube and a condenser were attached to the flask, and the mixture was refluxed for 2 hours to synthesize a hydroxyl group-containing polyimide.
- 10.5 g (0.05 mol) of maleimide hexanoic acid manufactured by Tokyo Kasei Co., Ltd. was added, and the mixture was further refluxed for 12 hours.
- 300 mL of toluene was added to the flask, and impurities were precipitated and removed by allowing to stand.
- the obtained solution is filtered through a glass frit funnel filled with silica gel, the solvent is removed by vacuum, and the following formula (1) is amber wax-like, having an imide skeleton in the main chain and a maleimide group in the side chain.
- the reactive resin 2 represented by -2) was obtained.
- the obtained reactive resin 2 was measured by a gel permeation chromatography (GPC) method using THF as an eluent and HR-MB-M (trade name, manufactured by Waters) as a column, and the weight average molecular weight was 30,000. there were.
- Reactive Resin 3 250 mL of toluene was put into a 500 mL round bottom flask containing a Teflon (registered trademark) stirrer. Then, 35 g (0.35 mol) of triethylamine and 35 g (0.36 mol) of anhydrous methanesulfonic acid were added and stirred to form a salt. After stirring for 10 minutes, 28 g (0.05 mol) of dimer diamine (Priamine 1075 manufactured by Claude), 4.5 g (0.05 mol) of 1,3-diamino-2-propanol, and pyromellitic anhydride 21. 8 g (0.1 mol) was added in this order.
- Teflon registered trademark
- a Dean-Stark tube and a condenser were attached to the flask, and the mixture was refluxed for 2 hours to synthesize a hydroxyl group-containing polyimide.
- 200 g of a large excess of butyl vinyl ether (manufactured by Tokyo Kasei Co., Ltd.) and 0.1 g of a palladium acetate phenanthroline complex were added to the flask, and the mixture was refluxed at 60 ° C. for 14 hours.
- Excess butyl vinyl ether was distilled off by an evaporator. After cooling to room temperature, 300 mL of toluene was added to the flask, and impurities were precipitated and removed by allowing to stand.
- the obtained solution is filtered through a glass frit funnel filled with silica gel, the solvent is removed by vacuum, and the following formula (1) is amber wax-like, having an imide skeleton in the main chain and a vinyl ether group in the side chain.
- the reactive resin 3 represented by -3) was obtained.
- the obtained reactive resin 3 was measured by a gel permeation chromatography (GPC) method using THF as an eluent and HR-MB-M (trade name, manufactured by Waters) as a column, and the weight average molecular weight was 30,000. there were.
- Reactive Resin 4 250 mL of toluene was put into a 500 mL round bottom flask containing a Teflon (registered trademark) stirrer. Then, 35 g (0.35 mol) of triethylamine and 35 g (0.36 mol) of anhydrous methanesulfonic acid were added and stirred to form a salt. After stirring for 10 minutes, 28 g (0.05 mol) of dimer diamine (Priamine 1075, manufactured by Claude), 7.6 g (0.05 mol) of 3,5-diaminobenzoic acid, and 21.8 g (0 mol) of pyromellitic anhydride. .1 mol) was added in this order.
- Teflon registered trademark
- a Dean-Stark tube and a condenser were attached to the flask, and the mixture was refluxed for 2 hours to synthesize a carboxylic acid-containing polyimide. After cooling the reaction mixture to room temperature, 300 mL of toluene was added to the flask, and impurities were precipitated and removed by allowing to stand. The obtained solution is filtered through a glass frit funnel filled with silica gel, and then 13.3 g (0.05 mol) of diallyl monoglycidyl isocyanurate (manufactured by Shikoku Kasei) and 3 g (0.3 mol) of triethylamine are added. It was heated for 3 hours.
- the obtained reactive resin 4 was measured by a gel permeation chromatography (GPC) method using THF as an eluent and HR-MB-M (trade name, manufactured by Waters) as a column, and the weight average molecular weight was 35,000. there were.
- a Dean-Stark tube and a condenser were attached to the flask, and the mixture was refluxed for 2 hours to synthesize a carboxylic acid-containing polyimide.
- 300 mL of toluene was added to the flask, and impurities were precipitated and removed by allowing to stand.
- the obtained solution was filtered through a glass frit funnel filled with silica gel, 4.2 g (0.02 mol) of maleimide hexanoic acid and 3 g (0.3 mol) of triethylamine were added, and the mixture was further heated for 3 hours.
- the solvent was removed by vacuum after cooling to room temperature to obtain a reactive resin 5 represented by the following formula (1-5), which was amber wax-like and had an imide skeleton in the main chain and a maleimide group in the side chain. ..
- the obtained reactive resin 5 was measured by a gel permeation chromatography (GPC) method using THF as an eluent and HR-MB-M (trade name, manufactured by Waters) as a column, and the weight average molecular weight was 35,000. there were.
- Reactive Resin 6 250 mL of toluene was put into a 500 mL round-bottom flask containing a Teflon (registered trademark) stirrer. Then, 35 g (0.35 mol) of triethylamine and 35 g (0.36 mol) of anhydrous methanesulfonic acid were added and stirred to form a salt. After stirring for 10 minutes, 31.9 g (0.06 mol) of dimer diamine (Priamine 1075, manufactured by Claude), 14.7 g (0.04 mol) of Bis-AP-AF, and 21.8 g (0. 1 mol) was added in this order.
- Teflon registered trademark
- a Dean-Stark tube and a condenser were attached to the flask, and the mixture was refluxed for 2 hours to synthesize a carboxylic acid-containing polyimide.
- 300 mL of toluene was added to the flask, and impurities were precipitated and removed by allowing to stand.
- the obtained solution was filtered through a glass frit funnel filled with silica gel, 16.9 g (0.08 mol) of maleimide hexanoic acid and 3 g (0.3 mol) of triethylamine were added, and the mixture was further heated for 3 hours.
- the solvent was removed by vacuum after cooling to room temperature to obtain a reactive resin 6 represented by the above formula (1-5), which was amber wax-like and had an imide skeleton in the main chain and a maleimide group in the side chain. ..
- the obtained reactive resin 6 was measured by a gel permeation chromatography (GPC) method using THF as an eluent and HR-MB-M (trade name, manufactured by Waters) as a column, and the weight average molecular weight was 35,000. there were.
- Reactive Resin 7 250 mL of toluene was put into a 500 mL round bottom flask containing a Teflon (registered trademark) stirrer. Then, 35 g (0.35 mol) of triethylamine and 35 g (0.36 mol) of anhydrous methanesulfonic acid were added and stirred to form a salt. After stirring for 10 minutes, 42.5 g (0.08 mol) of dimer diamine (Priamine 1075, manufactured by Claude), 7.3 g (0.02 mol) of Bis-AP-AF, and 21.8 g (0.02 mol) of pyromellitic anhydride. 1 mol) was added in this order.
- Teflon registered trademark
- a Dean-Stark tube and a condenser were attached to the flask, and the mixture was refluxed for 2 hours to synthesize a carboxylic acid-containing polyimide.
- 300 mL of toluene was added to the flask, and impurities were precipitated and removed by allowing to stand.
- the obtained solution was filtered through a glass frit funnel filled with silica gel, and then GO-BVE (glycidyloxybutyl vinyl ether, manufactured by Nippon Carbide) 8.6 g (0.04 mol) and triethylamine 3 g (0.3 mol). ) was added, and the mixture was further heated for 3 hours.
- GO-BVE glycidyloxybutyl vinyl ether, manufactured by Nippon Carbide
- the solvent was removed by vacuum after cooling to room temperature to obtain a reactive resin 7 represented by the following formula (1-6), which was amber wax-like and had an imide skeleton in the main chain and a vinyl ether group in the side chain. ..
- the obtained reactive resin 7 was measured by a gel permeation chromatography (GPC) method using THF as an eluent and HR-MB-M (trade name, manufactured by Waters) as a column, and the weight average molecular weight was 35,000. there were.
- Reactive Resin 8 250 mL of toluene was put into a 500 mL round-bottom flask containing a Teflon (registered trademark) stirrer. Then, 35 g (0.35 mol) of triethylamine and 35 g (0.36 mol) of anhydrous methanesulfonic acid were added and stirred to form a salt. After stirring for 10 minutes, 42.5 g (0.08 mol) of dimer diamine (Priamine 1075, manufactured by Claude), 7.3 g (0.02 mol) of Bis-AP-AF, and 21.8 g (0. 1 mol) was added in this order.
- Teflon registered trademark
- a Dean-Stark tube and a condenser were attached to the flask, and the mixture was refluxed for 2 hours to synthesize a carboxylic acid-containing polyimide.
- 300 mL of toluene was added to the flask, and impurities were precipitated and removed by allowing to stand.
- the obtained solution was filtered through a glass frit funnel filled with silica gel, and then DA-MGIC (diaminomonoglycidyl isocyanurate, manufactured by Shikoku Kasei Co., Ltd.) 10.6 g (0.04 mol) and triethylamine 3 g (0.3 mol). ) was added, and the mixture was further heated for 3 hours.
- the solvent was removed by vacuum after cooling to room temperature to obtain a reactive resin 8 represented by the following formula (1-7), which was amber wax-like and had an imide skeleton in the main chain and an allyl group in the side chain. ..
- the obtained reactive resin 8 was measured by a gel permeation chromatography (GPC) method using THF as an eluent and HR-MB-M (trade name, manufactured by Waters) as a column, and the weight average molecular weight was 35,000. there were.
- DA-MGIC diaminomonoglycidyl isocyanurate, manufactured by Shikoku Kasei Co., Ltd.
- the solvent was removed by vacuum after cooling to room temperature to obtain a reactive resin 9 represented by the following formula (1-8), which was an amber solid and had an imide skeleton in the main chain and an allyl group in the side chain.
- the obtained reactive resin 9 was measured by a gel permeation chromatography (GPC) method using THF as an eluent and HR-MB-M (trade name, manufactured by Waters) as a column, and the weight average molecular weight was 35,000. there were.
- GPC gel permeation chromatography
- an ethyl acetate solution of a functional group-containing (meth) acrylic polymer having a solid content of 55% by weight and a weight average molecular weight of 500,000 was obtained.
- a functional group-containing (meth) acrylic polymer having a solid content of 55% by weight and a weight average molecular weight of 500,000 was obtained.
- 2-isocyanatoethyl methacrylate was added as a functional group-containing unsaturated compound to react.
- Acrylic reactive resin was obtained.
- the obtained acrylic reactive resin was measured by gel permeation chromatography (GPC) using THF as an eluent and HR-MB-M (trade name, manufactured by Waters) as a column, and the weight average molecular weight was 55. It was ten thousand.
- Example 1 In 150 mL of toluene, 100 parts by weight of reactive resin 1, 0.3 parts by weight of bifunctional silicone acrylate (EBECRYL350 manufactured by Daicel Ornex) as a silicone compound, and 1 part of Irgacure 369 (BASF) as a photopolymerization initiator.
- a toluene solution of the pressure-sensitive adhesive composition was prepared by adding parts by weight.
- the obtained toluene solution of the pressure-sensitive adhesive composition was applied to a corona-treated surface of a 25 ⁇ m-thick polyimide film (Kapton, manufactured by Ube Industries, Ltd.) having a corona treatment on one side so that the thickness of the dry film was 40 ⁇ m.
- a corona-treated surface of a 25 ⁇ m-thick polyimide film Kerpton, manufactured by Ube Industries, Ltd.
- Example 2 to 20 Comparative Examples 1 to 3
- the pressure-sensitive adhesive composition and the pressure-sensitive adhesive tape were prepared in the same manner as in Example 1 except that the types and amounts of the reactive resin, polyfunctional monomer, silicone compound or fluorine compound, and photopolymerization initiator were as shown in Tables 1 and 2. Obtained.
- a hexafunctional silicone acrylate (EBECRYL1360 manufactured by Daicel Ornex) was used as the silicone compound.
- Example 9 and Comparative Example 1 a photoreactive fluorine compound (Megafuck RS-56, manufactured by DIC Corporation) was used as the fluorine compound.
- Example 15 5-phenyl-1H tetrazole (manufactured by Masuda Chemical Co., Ltd.) was used as the gas generating agent, and 9,10-diglycidyloxyanthracene (manufactured by Kawasaki Kasei Chemicals Co., Ltd.) was used as the photosensitizer.
- the obtained adhesive tape was cut into a width of 1 inch and then heat-laminated on 1 mm thick glass with a laminator at 100 ° C. After laminating, ultraviolet rays of 365 nm were irradiated from the glass side at an intensity of 20 mW / cm 2 for 150 seconds using an ultra-high pressure mercury lamp. After irradiation with ultraviolet rays, the glass side was heated on a hot plate at 300 ° C. for 10 minutes. The adhesive strength (N / inch) was measured by performing a 180 ° peel test on the test piece after laminating, after irradiation with ultraviolet rays, and after heating at 300 ° C. under the conditions of 25 ° C. and a tensile speed of 30 mm / sec. ..
- an adhesive composition which can be easily peeled off by irradiating light even after undergoing a high temperature processing treatment of 300 ° C. or higher with the adherend fixed. It is possible to provide an adhesive tape having an adhesive layer composed of a composition, and a method for processing an electronic component.
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- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Polymers & Plastics (AREA)
- Medicinal Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Condensed Matter Physics & Semiconductors (AREA)
- Microelectronics & Electronic Packaging (AREA)
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CN202080020403.6A CN113574083A (zh) | 2019-03-20 | 2020-03-19 | 粘合剂组合物、粘合带及电子部件的处理方法 |
KR1020217017753A KR20210144654A (ko) | 2019-03-20 | 2020-03-19 | 점착제 조성물, 점착 테이프, 및 전자 부품의 처리 방법 |
JP2020529778A JP7433228B2 (ja) | 2019-03-20 | 2020-03-19 | 粘着剤組成物、粘着テープ、及び、電子部品の処理方法 |
US17/439,576 US20220162480A1 (en) | 2019-03-20 | 2020-03-19 | Adhesive composition, adhesive tape, and method for processing electronic component |
JP2024016391A JP2024036541A (ja) | 2019-03-20 | 2024-02-06 | 粘着剤組成物、粘着テープ、及び、電子部品の処理方法 |
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